Part of the premise for this episode is that Homer is having a mid-life crisis, having spent 20 years in the same house, with the same car, and the same job as noted by Marge. This comes after seeing how pathetic Kirk VanHouten looks trying to act half his age. But how can Homer be upset over this? He’s always done whatever he wants, and that includes numerous crazy stunts and weird jobs.

But somehow he’s stuck in a rut?

Whatever.

Point is, Homer is, and that causes him to dig up letters to his childhood pen pal, a boy named Eduardo from Spain. Homer had the choice between a foreigner or a prisoner, and he chose a foreigner because he figured he wouldn’t have to reply so often. Marge, being a good wife, gets the idea to invite Eduardo to Springfield to cheer Homer up. And since Eduardo is a man who’s lived a very satisfying life with 8 wives and 200 children, none of whom are disrespectful punks who call their father by his first name, he’s got it all. He also saved all of Homer’s letters and decided to help Homer live out as many of his childhood dreams as he possibly can (striking out Jesus in the World Series is out).

But he can be a pirate! He and Eduardo crash a dinner theater production of Pirates of Penzance, much to the displeasure of the director, Llewellyn Sinclair (yup, Jon Lovitz for a couple lines).

Meanwhile, there’s a cheating scandal at Springfield Elementary, and Lisa suggests they implement an honor code where students will monitor each other for cheaters. That works until Lisa finds out Bart is cheating, and that’s because he realized the loophole that if Lisa’s brother is cheating and she reveals it, she proves the system doesn’t work. Can Lisa convince Bart to turn himself in?

Maybe with a divine sign.

That would be when Homer tumbles out of the sky when the wing suit he was using with Eduardo can’t cope with repeated hits to the tallest building in Springfield. He lands on top of Bart, and that sure is a divine sign.

After that, Eduardo is set to go home and asks Homer to take him to the airport. How far should Homer take him? Eduardo suggests Homer take him as far as his heart will take him. As such, Homer escorted Eduardo back to Spain. Homer’s a good friend.

By the way, Marge’s childhood dream was jumping on the bed. She got to live that out too.